“So I was wondering if you would do me another favor.”….

…continued

“Well, considering what you asked for last time, this should be interesting.”

Ruth gave a little chuckle and said: “I guess I have been asking quite a bit of you, never mind.”

I got the feeling that Ruth was feeling a bit hurt. “No, I didn’t mean it like that, I was just saying that we keep going further every time we get together.”

“Oh, yes, well I guess that may be the case here, too. My granddaughter comes over quite often, and we visit for a few hours every week. Her mother tends to be very quiet and reserved, so I have ended up being the person Carrie goes to with all her questions and problems. We talk about pretty much everything, and I don’t keep any secrets from her.”

I was a bit curious at this point to see where she was going with this, but I remained quiet and let her continue as I drove.

“A couple weeks back when I dyed my hair, she asked me why I did it in such a bright color. I tried to tip-toe around the subject and just told her that there was a man whose attention I was trying to get. Carrie wouldn’t let it rest at that, and she was asking me if it worked and why the family had not met my new boyfriend. I told her that you were not that kind of boyfriend, but apparently that just raised more questions. I had the birds and the bees talk with her a couple of years ago but apparently her mother has told her that she shouldn’t even be thinking of such things, and she must wait until she is married. So she was a bit confused when I told her that I had a man that I just have sex with. Then she asked me why I didn’t just pretend we were having a serious relationship and show you to the family anyway.”

I pretty much froze when she said that, but luckily she continued;

“Then I told her how old you are and explained that physical relationships can be taboo and break rules that other people wouldn’t be happy about. Then the conversation finally came off of us and Carrie wanted to talk about herself. She told me that she was a virgin and was having second thoughts about what her mother had been telling her. She said that her classmates in high school,…… she just turned eighteen two weeks ago by the way,…. spread gossip all the time and she didn’t feel comfortable with any of the boys she knew. She would tell me about all the sexual things her friends would tell her, and how she desperately wanted to experience those things for herself.”

Now I was back to being curious, and a little turned on.

“She asked me if I thought it was alright for her to have a physical relationship with a guy, and I told her I didn’t see much problem with it as long as she wasn’t jumping into bed with a bunch of different guys, made sure to use a condom AND use birth control. As soon as I told her that, she said she didn’t have any guys in mind, so she asked me if I would share my boyfriend! I was shocked when she said that, and I said there was no way I would set you up with her. She said she didn’t want to date you, she figured you had to be the type of guy I would approve of if I was already with you. I told her it wasn’t right for two women to be treating a man like a time-share, and she turned my earlier comment about taboos around on me. Then she told me she didn’t want to share, she wanted to join in, like on a threesome!”

My head just about exploded at this point. We pulled up to Ruth’s house and I shut off the car. I put my face in my hands and rubbed my eyes as I tried to wake up from this bizarre hallucination I was having. I had just finished servicing the 95 year old mother of my current sex partner, and now she is suggesting that I take a run at the third of four generations of her family.

‘So what do you think?” Ruth asked.

I just sat there for a moment wondering what to do. I think I already knew what I was going to do, but maybe I was just imagining how to go through with it. “What did you have in mind?”

Ruth smiled, “Well I basically just want you to pop her cherry. I want her to enjoy herself, but I want her to learn the basics, along with a few special things. I want her to know how to please a man, and I want you to have a good time, but I was hoping you could do a few favors for her as well. Don’t worry, I will be walking her through it, and I will be participating to make sure you get what you need. I may demonstrate a few things as well. She said as she grinned and opened her door. I’ll go set this up for next week, she’s inside waiting for me.” She said as she pointed to the car parked in front of us.

I watched her go into the house and then I drove off, thinking about next week.

I made my deliveries to her for the next few days. Ruth told me that she wanted to do it on Thursday night, and then we started to chat about different things that she wanted to make happen for Carrie’s magical night. Ruth seemed to be as excited as she would if it was her first time.

Thursday rolled around and I found myself just a little nervous as I made my way up to the front door. I rang the bell and Ruth answered the door. She led me into the living room where there were blankets and pillows spread out on the floor to make a comfortable area for the intimate encounter. Carrie was seated on the couch, sinning on her hands. I could tell she was far more nervous than I was. Ruth told me not to expect her to talk much, if any.

Carrie stood as we approached her, and she forced a smile as she looked over the man that was supposed to deflower her. Her face was cute enough, but her body really made me wonder how she could still be a virgin. She stood less than five and a half feet tall, and not much more than a hundred pounds. She had a very thin waist that was offset by C cup breasts. I looked back up to her face which was blushing heavily as she looked everywhere but at me.

I figured it would make her even more uncomfortable to just start taking her clothes off, so I turned to Ruth and started to unbutton my shirt. I didn’t say anything as I let it slide off of my arms and I tossed it onto a chair nearby. I walked up to Ruth and started to unbutton her blouse. I opened it up and slid it up and off her shoulders. I figured we didn’t need to fondle much if this experience was going to be all about academics. I reached behind her and unhooked her bra, releasing her heaving breasts from their cups.

Now that the two of us were half naked, I figured I could start in on Carrie without her fainting. I walked up behind her and started to rub her arms up and down. I pressed myself against her as I moved my hands down to her hips. I lightly ran my fingers over her body, and I could see goose bumps forming on her arms. I stroked over her stomach and down to the front of her pants. As I worked my way back up, I hooked my fingers under her tight cotton top and started to pull it up. Carrie put her arms up and let me slide it all of the way up and off of her. I brought my hands back and continued to caress her body.

I leaned in and started to nibble on her ear lobe as I worked my hands over her warm skin. I moved down to the waist of her jeans and popped open the button at the top. As I lowered the zipper on her pants, I looked up towards Ruth, who had removed her skirt and was taking off her panties. She sat down in a chair facing us and started to rub her pussy. Carrie opened her eyes to see her grandma masturbating in front of her. I immediately felt her relax a bit and she put her hands on the back of mine. We slid her jeans off and she stepped out of them. I led her to the middle of the room and laid her down on the blanket.

I got down in front of her, between her legs and hooked my finger into the waist of her thong and slipped it off. I didn’t feel the need to fondle any more, because Carrie was feeling good now. I pulled her lips apart and gazed upon her hot, tight pink entry. I put my thumb to her clitoris and started to work it in a circular motion.

Carrie laid her head back as I manipulated her button and started her on her journey. I pulled her lips further apart as I moved in and brought my tongue down to her clit. I started to flick and stroke her now enlarged button. Carrie almost instantly started to squeeze my head with her thighs as waves of ecstasy started to crash over her body. I sat back and continued to massage her button with my thumb. I used the middle finger on my other hand to probe around her love hole. I brought my finger up to my mouth and wet it down.

Once back at her entrance I gently pushed it inside of her bit by bit. Now in up to the second knuckle, I curved it up and felt that ridged area on the front wall of her canal. I slid my fingertip over that washboard and in no time at all, Carrie’s juices were flowing. I moved both of my hands into a rhythm and after just a few minutes, she was screaming from her first climax. As Carrie was coming down, Ruth had snuck up behind me and tapped me on the shoulder. She motioned for me to back away, because she wanted to change out. I moved over and Ruth quickly replaced my thumb on her granddaughter’s clit and then I slipped my finger out of her vagina.

I got up and out of my pants and boxers. I started to stroke my penis to get it to full strength as I watched the incestuous lesbian action going on in front of me. Ruth went in with her tongue and lapped up the juice that was dripping from the virgin hole. Carrie was on her way right back up to another peak. She started to quake once again and continued to jerk around as her grandma worked her cunt furiously.

I wasn’t content to stand there and watch the action. I decided to kill a little time behind Ruth. I came in behind of her and pointed my head towards her entrance. I decided to give both of them a quick surprise. I plunged my dick all of the way into her wet pussy in one shot. Ruth let out a little squealing moan, and that snapped Carrie out of her trance. She lifted her head and looked down to find her granny between her legs. Carrie started to get up to her elbows and looked quite startled. As Ruth kept teasing her clitoris with her mouth, Carrie began relaxing once again and laid back once more.

I started to hump Ruth while she had her face buried. I guess I was getting a little more of a visual treat than normal, because I felt like I was ready to finish in short order. I could feel my balls start to tighten, and I had to pull out quickly. As I got up from Ruth, she stood up from Carrie. Ruth said it was time for her to learn how to repay the favor. I sat down on the couch and started to squeeze hard on my shaft to reset the stopwatch on my climax. Ruth had Carrie sit down next to me as she got down between my legs.

She grabbed the shaft and pinned it up against my stomach. Ruth started by licking my scrotum and taking my testicles into her mouth one at a time and then both at once. I watched her cheeks bulge out as she rolled them around in her mouth. After Ruth released them from her mouth, she licked the excess saliva off and started to lick up the bottom side of my dick.

I reached over and started to pet Carrie’s bald pussy as she watched her granny give me oral sex. Ruth let my cock come straight out and started to circle the head with her tongue. She put her lips to the tip and started to suck on just the head. Slowly she started to stroke up and down, gradually taking more of my length into her mouth. She repositioned herself further down pulling my penis down with her so it was aimed better for what she wanted to show off next. Ruth tipped her head back and slid me deep into her throat until she was down to the root of my shaft. She gave it a few strokes and then released me from her mouth.

She got up and took Carrie’s hand standing her up. I gave my dick another good squeeze to soften it up a bit. Carrie knelt down in front of me and grasped my member with her hand and stroked it a few times. She seemed a bit hesitant and didn’t want to start. Ruth got down next to her and started rubbing her back with one hand as stroked my thigh with the other. Her hand moved from Carrie’s back down to her ass, and then in between her legs. Once she rubbed her pussy a bit, Carrie finally put her mouth down to my penis. She flicked her tongue at the tip of my penis and then flattened it out and started making long strokes down the top of it. She flipped it back and started licking the bottom.

I put my hand on the back of her head and gave it a little rub. I think it got the message across, because she finally started to suck on the tip. She was sucking hard and rubbing the head with her tongue. I started to push her head down and got her to start stroking at a slow tempo. As I got deeper into her mouth, she began raking her teeth over my shaft on the upstroke. She wasn’t able to deep throat me, but after a few minutes she was performing like a pro. After about ten minutes I had her stop so I could get a little breather.

Carrie backed away and I got up, taking Ruth’s hand. I had her lay back on the blanket in the middle of the floor. I turned to Carrie and reached behind her unhooking her skimpy little bra. She slipped her arms out of it and I got a look at her good sized, firm breasts. I led her over to her granny and had her get down in between Ruth’s legs. Once again, she seemed a little hesitant, but she knew what she was supposed to do. I figured she would be less nervous if I wasn’t watching her, so I got down next to Ruth and started sucking on her nipple.

Carrie starting in on her grandma’s pussy and Ruth was moaning in no time. I am sure she was enjoying the twist that it was her own flesh and blood eating her out. I got up and moved next to Carrie. I started to pinch on her nipple and put my other hand around behind her. She seemed to be doing a good job on granny’s cunt as I moved behind her. I started to stroke my fingers through her pussy lips. I pulled her ass cheek open and dropped my spit onto her anus. I spread it around with my thumb as I continued playing with her pussy with the other hand. I slipped my thumb into her ass and joined the rhythm that she was using on her grandma.

I started furiously rubbing her cunt, focusing on her button. She started to quiver and was forced to stop her oral experiment. I plunged my thumb deep into her and pressed hard into her clit, causing her to gasp and collapse to her side as her whole body seized. I took my hands away as she flopped onto her side. After a few breaths, she crawled over to the couch and said she needed a little break. Ruth was still on her back, so I just hopped on. I got on top and started railing furiously into her. I ground my pelvis against her clit as I pumped into her. Ruth started to scream as her orgasm crashed over her. She clamped down hard on my dick and wrapped her legs around me, stopping me from thrusting any more.

Ruth let me go, and I slid out of her vagina. I grabbed her leg and rolled her over onto her stomach. I pulled her legs together and straddled them. My dick was slick with her juices. I pulled her cheeks apart and put my head to her asshole. I slowly pressed forward, but was able to get all of the way in easily. I leaned forward, laying on top of her and sliding my hands underneath her breasts. I twisted on her nipples as I humped into her ass. Ruth squeezed her anus on the out stroke, milking me, trying to get me off. I could feel myself getting weak, approaching my climax. I slowed down to hold off my finish, but Ruth would not hear of it. She started to twist her ass, stroking me deeper into her. I had to pull out and take a break.

I got up and flipped Ruth onto her back once again. I motioned for Carrie to come back over. I got her down between Ruth’s legs and grabbed her hand. Her hands were a lot smaller than mine so I squeezed her fingers together and put her hand down to grandma’s love hole. I let go of her fingers and grabbed her wrist, pushing her hand all of the way inside. I let go and got up, taking a seat on the couch. I had to make sure not to touch myself as I watched the extremely erotic scene in front of me. I didn’t want to finish myself off. My jaw gradually dropped open as I gazed at the bizarre spectacle in front of me.

Carrie began pumping her arm in faster and faster. Ruth began to scream with yet another orgasm as she clamped down on the young girl’s wrist. She released her hold on Carrie’s hand and let her pull it out of her tender pussy. She let out a little moan of discomfort as the largest part came back out. Ruth just laid there for a few minutes, catching her breath. She was the only one who had not taken a break yet. Once she had her strength back, she rolled over and crawled to the end table, where there were a few condoms. She grabbed one and crawled over to me.

Ruth grasped my penis and stroked it a few times, making sure it was good and hard. She tore the condom wrapper open and pulled out the rubber. After placing it in her mouth, she turned to Carrie to show her how to hold it between her lips and teeth. She turned back to me and slowly deep throated my shaft, unrolling the entire length of the condom. She came back up and motioned to Carrie for her to lay on her back on the blanket. Then Ruth got up and sat on the couch, pushing me off of it. She looked like she was done for the night.

I got up and walked to the end table, grabbing the bottle of lubricant that was next to the condoms. I got down between Carrie’s legs and gave myself a few strokes. I opened the bottle and put some lube on my fingers. I rubbed them on her entrance and a little inside of her hole as well. Then I squeezed some more onto my cock and spread it around. I tossed the bottle off to the side and repositioned myself. I spread her legs and put my penis at her entrance. I pressed it against her tight hole and she offered a lot of resistance. I was hard as a rock, so I didn’t need to guide my penis. I leaned forward and pressed myself against her.

Slowly I pushed forward, and little by little I was granted passage into her canal. She looked to be in a bit of pain, so I backed out and started my stroke again. I kept a very slow rhythm, and eventually I was all of the way inside this no longer virgin vagina. Now that I was all the way in, Carrie seemed to be a lot more comfortable. We kept it slow, but she was able to twist her pelvis and bury me deep inside of her. Quickly she got the technique down and was taking it like her old granny did. I shifted my position to get a better stroke on her g-spot, and Carrie started to moan with every stroke.

I put my face down next to her head, and worked my hands under her back, hooking them back up onto her shoulders. I started to thrust in harder, slapping our bodies together. Carrie took after granny, and wrapped her legs around my waist as she reached her orgasm. She held on tight and grabbed my shaft even tighter. The tight squeeze didn’t do much to hold off my orgasm, but I didn’t want to blow my load into a rubber. I got up and rolled the blood soaked condom off of my penis. I squeezed a little lube onto my bare cock, and spread it out with two fingers.

I grabbed Carrie’s thigh and rolled her over onto her stomach. Then I scooped my arm underneath her hips and pulled her up onto her knees. I took the two fingers that still had lube on them and spread what was left around her anus. I still felt ready to blow, so I didn’t plan to last very long. I laid the head of my penis on her rose bud , which was currently covered in blood. I hopped up to my feet to get a good angle, and pressed down against her exit. To my surprise, the head of my penis popped inside easily. I pushed in slowly and pulled back, once again working my way in stroke by stroke. This time it took a bit longer, but I was finally able to get in almost all the way.

Her anus seemed to spasm without warning and was actually holding me off pretty well. I grabbed a hold of her hips and started to ride. I dropped back down to my knees and let her ass pound back onto my thighs as I thrust away. I could feel my climax coming on again and this time I was finally going to finish. My legs got weak as I started to erupt inside of her ass. I used my arms to keep pulling her onto me as I shot load after load deep up inside of her. I started to slow down and after ten or twelve shots I was completely drained. I slowly withdrew my cock from her now gaping asshole. My cum leaked out and just like her grandma, she tightened up her sphincter, and started to shit out little wads of my seed.

I put my hand under her hole and scooped up all of the spent semen. When she was done she rolled over, too tired to do much else. I took the handful of cum and rubbed it all over her breasts. Ruth hopped down off of the couch and laid down next to her. She stuck out her tongue and licked up a large wad of my sticky mess from Carrie‘s breast, and then moved up and planted a kiss on Carrie’s lips, spitting my seed into her mouth. I sat back and reflected on the night’s activities as I watched these two family members tongue wrestling each other with my semen dripping from the corners of their mouths.